Executive Assistant
How to Use These Prompts
For best results, copy and paste the prompt into your preferred large language model (like ChatGPT or Claude AI or Gemini). Replace the bracketed text [like this] with your specific details. The more context you provide, the more tailored and insightful the AI’s response will be.
Category 1: Strategic Calendar & Time Management
1. The Ideal Week Architect:
“Act as a strategic operations consultant. My executive’s key priorities for this quarter are [Priority 1: e.g., Close Series B funding], [Priority 2: e.g., Recruit a VP of Engineering], and [Priority 3: e.g., Launch new product feature]. Design an ‘ideal week’ template for their calendar. Block out time for deep work, strategic planning, 1:1s with direct reports, team meetings, and external stakeholder engagement. Provide a brief justification for the structure and flow of the week.”
2. Meeting Request Gatekeeper & Scripter:
“Generate a set of three email templates for managing my executive’s meeting requests. The tone should be polite but firm, protecting their time. Create one template for politely declining a non-essential meeting, one for redirecting the request to a more appropriate person on the team, and one for requesting a detailed agenda and objectives before accepting a meeting.”
3. Proactive Deconfliction & Rescheduling:
“An urgent, high-priority meeting with [New High-Priority Attendee] must be scheduled for next week. My executive’s calendar is completely booked. Identify the two lowest-priority meetings that could be rescheduled. Draft a concise and respectful email to the attendees of the meeting to be moved, explaining the need to reschedule (without revealing confidential details) and offering two alternative time slots.”
4. Calendar Audit for Burnout Prevention:
“Analyze the following schedule from last week: [Paste a sanitized version of the executive’s calendar, e.g., ‘Monday: 8 AM-9 AM – Sales Sync; 9 AM-11 AM – Investor Pitch Prep…’]. Identify patterns that could lead to burnout, such as back-to-back meetings without breaks, insufficient deep work time, or an overload of low-impact status updates. Suggest 3-4 actionable changes to create a more sustainable and productive schedule.”
5. Multi-Time-Zone Trip Scheduling:
“My executive is traveling to [City, Country] for 3 days. Their home time zone is [e.g., EST], and the destination is in [e.g., CET]. The trip’s purpose is to [e.g., meet with the European sales team and visit key clients]. Create a detailed meeting schedule that strategically groups meetings by location, minimizes travel time within the city, and intelligently schedules calls with the home office to respect both time zones. Indicate which meetings should be prioritized if the schedule becomes tight.”
Category 2: Masterful Communication & Inbox Management
6. Executive Voice Email Drafting:
“Analyze the following three emails written by my executive: [Paste 3 sanitized, representative email samples] to understand their tone, vocabulary, and sentence structure. Now, draft an email from them to the entire company announcing [e.g., a new remote work policy update]. The email should be clear, empathetic, and reflect their established communication style.”
7. Inbox Triage & Action Plan:
“Act as an inbox manager. Here is a list of 10 subject lines and senders from my executive’s inbox: [List 10 sanitized subject lines, e.g., ‘Update on Project Phoenix – CEO of PartnerCo’, ‘Quick Question – Junior Analyst’, ‘Your Expense Report – HR’, etc.]. Triage these into four categories: ‘For Executive’s Immediate Attention,’ ‘For Me (EA) to Handle,’ ‘For Executive to Read Later,’ and ‘For Deletion/Archive.’ Provide a one-sentence action plan for each email I need to handle.”
8. Daily Executive Briefing Template:
“Create a template for a ‘Daily Briefing’ email I can send my executive each morning. The template should have five sections: 1) Today’s Top 3 Priorities, 2) Critical Reminders & Deadlines, 3) Detailed Schedule with Key Meeting Objectives, 4) Awaiting Your Response (items I need their input on), and 5) For Your Information (FYI).”
9. Stakeholder Communication Matrix:
“We are beginning a new initiative: [e.g., an office relocation project]. Key stakeholders include [The Leadership Team], [All Employees], [Building Management], and [External Vendors]. Create a communication matrix in a table format. Columns should be: Stakeholder Group, Key Message, Communication Method (e.g., Email, Slack, In-Person Meeting), Frequency, and Owner. This will ensure everyone stays informed.”
10. Pre-Meeting Talking Points for Difficult Conversations:
“My executive has a meeting with [Person’s Name/Team] to discuss [a sensitive topic, e.g., a missed deadline on a critical project]. To prepare them, generate a list of talking points. The points should follow a structure: 1) Acknowledge their hard work, 2) State the problem clearly and objectively, 3) Ask open-ended questions to understand their perspective, and 4) Define clear, collaborative next steps.”
Category 3: Flawless Meeting & Event Execution
11. Results-Oriented Agenda Design:
“Create a results-oriented agenda for an upcoming 90-minute [e.g., Quarterly Marketing Strategy Meeting]. The desired outcome is to [e.g., finalize the Q4 budget and approve the top 3 campaign initiatives]. Instead of generic topics, frame each agenda item as a question to be answered or a decision to be made. Assign a time limit and a designated owner to each item.”
12. Action Item & Accountability Tracker:
“Following a project kickoff meeting, I have the following raw notes: [Paste a sanitized list of decisions and action items]. Convert these notes into a structured Action Item Log using a table. The columns should be: Action Item #, Task Description, Assigned Owner, Due Date, and Status (Not Started, In Progress, Complete). Draft a follow-up email to the attendees summarizing these action items and confirming ownership.”
13. The ‘One-Page’ Executive Pre-Briefing:
“Develop a one-page briefing document template for my executive ahead of any important external meeting. It should be skimmable and contain: 1) Attendee Bios (with LinkedIn links), 2) Company Overview, 3) Meeting Objectives (What do we want from this?), 4) Key Talking Points/Our Ask, 5) Potential Questions They Might Ask, and 6) Relevant History/Context.”
14. Comprehensive Offsite Project Plan:
“Generate a detailed project plan for a 2-day leadership team offsite for 15 people. The goal is [e.g., 2026 strategic planning]. The plan should be a timeline-based checklist, starting 8 weeks out from the event date, and include tasks for: Venue Selection, Budgeting, Agenda Development, Travel & Accommodation, Vendor Coordination (catering, A/V), and Post-Event Follow-up.”
15. Presentation Scaffolding & Narrative:
“My executive needs to create a 15-minute presentation for the board on [Topic: e.g., Q3 Performance Review]. Generate a 10-slide outline that tells a compelling story. Start with the ‘big picture’ conclusion, provide supporting data highlights, address a key challenge and how it’s being mitigated, highlight a major win, and end with a clear outlook for the next quarter. Suggest what data visualization (e.g., bar chart, trend line) would be most effective for each slide.”
Category 4: Proactive Executive Partnership & Automation
16. Standard Operating Procedure (SOP) Creation:
“Write a clear, step-by-step Standard Operating Procedure (SOP) for the process of [e.g., submitting and approving executive expense reports]. The document should be easy for a new team member to follow and include sections for: Objective, Tools Required, Step-by-Step Instructions, and Common Pitfalls to Avoid.”
17. Anticipatory Needs Checklist for Travel:
“My executive is confirmed for a 4-day trip to attend the [Conference Name] in [City]. Beyond booking flights and hotel, create a checklist of 10 proactive, high-value tasks I should complete to make the trip seamless and strategic. Include items like ‘Pre-schedule coffee meetings with key contacts attending,’ ‘Prepare a folder of relevant documents for offline access,’ and ‘Block out post-trip debrief time on the calendar.'”
18. Workflow Automation Audit:
“Act as a process improvement consultant. Here are 5 repetitive tasks I perform weekly: 1) Manually compiling a report from three data sources, 2) Sending reminder emails for deadlines, 3) Scheduling recurring team meetings, 4) Saving email attachments to a specific cloud folder, 5) Transcribing audio notes. For each task, suggest a specific automation tool (like Zapier, Microsoft Power Automate, or a scheduling tool feature) and briefly explain how it could automate the process.”
19. Executive Preference Profile Database:
“Design the structure for a comprehensive ‘Executive Preference Profile’ in a tool like Notion or a simple document. This profile should be the single source of truth for their professional preferences. Create sections and subsections for: Travel (airline, seat preference, loyalty numbers), Food & Beverage (allergies, coffee order, favorite restaurants for client dinners), Communication Style (preferred channel for urgent vs. non-urgent matters), and Key Contacts (names, titles, relationship context).”
20. Relationship Management Tracker:
“My executive needs to maintain strong relationships with their top 20 professional contacts. Create a simple CRM-style tracking table. Columns should include: Contact Name, Company, Title, Last Contact Date, Next Action (e.g., ‘Send follow-up email,’ ‘Schedule Q4 check-in’), and a ‘Notes’ section to log key personal details (e.g., ‘Daughter is applying to colleges,’ ‘Loves fly fishing’).”
Category 5: Data-Driven Decision Support
21. Concise Report Synthesis:
“I am providing you with a lengthy report: [Paste text of a dense, multi-page report or article]. Your task is to synthesize this document into a ‘Five-Point Briefing’ for my executive. It must include: 1) The single most important takeaway, 2) The three most critical supporting data points, and 3) One actionable recommendation based on the report’s findings.”
22. Competitive Software Analysis:
“We are considering a new tool for [e.g., project management]. Conduct a preliminary analysis of three leading competitors: [Software 1: e.g., Asana], [Software 2: e.g., Monday.com], and [Software 3: e.g., Trello]. Create a comparison table with the following rows: Key Features, Pricing Model, Ideal Use Case (e.g., best for creative teams), and a notable Pro/Con for each.”
23. Meeting Cost-Benefit Analysis:
“Help me draft a polite pushback for a recurring one-hour weekly meeting that my executive feels has low value. First, calculate the ‘cost’ of the meeting assuming 8 attendees with an average blended hourly salary of $[e.g., 150]. Then, draft a brief email to the meeting organizer that quantifies this cost and suggests reducing the frequency to bi-weekly or monthly, while handling interim updates via a shared document or email.”
24. Vendor Negotiation Talking Points:
“We need to renew our contract with a software vendor, [Vendor Name]. Our goal is to reduce our annual cost by 15%. Research common software negotiation tactics and generate a list of talking points for my executive to use on the call. Include points like leveraging our long-term partnership, referencing competitor pricing (if known), and asking for a multi-year discount.”
25. EA to Chief of Staff Professional Development Plan:
“Act as a career coach. I am an EA who aspires to grow into a Chief of Staff role within the next 2-3 years. Based on the typical responsibilities of a Chief of Staff (strategic planning, project management, serving as a proxy for the executive), create a professional development plan for me. Identify 3 key skills to develop, suggest specific online courses or certifications, recommend 2 relevant books to read, and propose one type of ‘stretch project’ I could ask to take on in my current role.”